Electronic Supplementary Information. Iridium(III) phosphors with bis(diphenylphorothioyl)amide ligand for
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1 Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C. This journal is The Royal Society of Chemistry 218 Electronic Supplementary Information Iridium(III) phosphors with bis(diphenylphorothioyl)amide ligand for efficient green and sky-blue OLEDs with EQE nearly 28% Jing-Cheng Xia 1, Xiao Liang 1, Zhi-Ping Yan 1, Zheng-Guang Wu 1, Yue Zhao 1, You-Xuan Zheng 1,2, * and Wen-Wei Zhang 1, * 1 State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Collaborative Innovation Center of Advanced Microstructures, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 2193, P. R. China, * - yxzheng@nju.edu.cn; wwzhang@nju.edu.cn 2 Shenzhen Research Institute of Nanjing University, Shenzhen 51857, P. R. China General information 1 H NMR spectra were measured on a Bruker AM 4 spectrometer. The high resolution electrospray ionization mass spectra (HR ESI-MS) were recorded on an Bruker MTQ III q-tof. TG measurements were carried out on a TG/DSC_STA449F3 analyzer (METTLER). UV-vis absorption and photoluminescence spectra were measured on a Shimadzu UV-255 and a Hitachi F-46 spectrophotometer at room temperature, respectively. Cyclic voltammetry measurements were conducted on a chi6e electrochemical workstation using Fc + /Fc as the internal standard and scan rate of.1 V s -1. X-ray crystallography X-ray crystallographic measurements of the single crystals were carried out on a Bruker SMART CCD diffractometer (Bruker Daltonic Inc.) using monochromated Mo Kα radiation (λ =.7173 Å) at room temperature. Cell parameters were retrieved using SMART software and refined using SAINT program to reduce the highly redundant data sets. Data were collected using a narrow-frame method with scan width of.3 in ω and an exposure time of 5 s per frame. Absorption corrections were applied using SADABS supplied by Bruker. The structures were solved by Patterson methods and refined by full-matrix least-squares on F 2 using the program SHELXS-97. The positions of metal atoms and their first coordination spheres were located from direct-
2 methods E-maps, other non-hydrogen atoms were found in alternating difference Fourier syntheses and least-squares refinement cycles and during the final cycles refined anisotropically. Hydrogen atoms were placed in calculated position and refined as riding atoms with a uniform value of U iso. OLEDs fabrication and measurement All OLEDs were fabricated on the pre-patterned ITO-coated glass substrate with a sheet resistance of 15 Ω sq -1. The deposition rate for organic compounds is 1-2 Å s -1. The phosphor and host were co-evaporated from two separate sources. The cathode consisting of LiF/Al was deposited by evaporation of LiF with a deposition rate of.1 Å s -1 and then by evaporation of Al metal with a rate of 3 Å s -1. The effective area of the emitting diode is.1 cm 2. The characteristics of the devices were measured with a computer controlled KEITHLEY 24 source meter with a calibrated silicon diode in air without device encapsulation. On the basis of the uncorrected PL and EL spectra, the CIE coordinates were calculated using a test program of the spectra scan PR65 spectrophotometer. Mass/% (ppy) 2 (tfppy) 2 (ttppy) 2 (tntppy) Temperature ( ) Fig. S1 The TG curves of Ir(ppy) 2 (Stpip), Ir(tfppy) 2 (Stpip), Ir(ttppy) 2 (Stpip) and Ir(tntppy) 2 (Stpip).
3 Current ( A) (ppy) 2 (tfppy) 2 (ttppy) 2 (tntppy) 2 Current ( A) (ppy) 2 (tfppy) 2 (ttppy) 2 (tntppy) Potential (V) Potential (V) Fig. S2 The cyclic voltammogram curves of Ir(ppy) 2 (Stpip), Ir(tfppy) 2 (Stpip), Ir(ttppy) 2 (Stpip) Ir(tntppy) 2 (Stpip) in degassed CH 2 Cl 2 solution at room temperature. and 5 4 (ppy) 2 ExpDecay Fit of (ppy) s 5 4 (tfppy) 2 ExpDecay Fit of (tfppy) s Counts 3 2 Counts Time ( s) Time ( s) 5 4 (ttppy) 2 ExpDecay Fit of (ttppy) s 5 4 (tntppy)2 ExpDecay Fit of (tntppy)2 1.5 s Counts 3 2 Counts Time ( s) Time ( s) Fig. S3 The lifetime curves of Ir(ppy) 2 (Stpip), Ir(tfppy) 2 (Stpip), Ir(ttppy) 2 (Stpip) and Ir(tntppy) 2 (Stpip) in degassed CH 2 Cl 2 solution at room temperature.
4 Normalized Intensity (a. u.) (ppy) 2 (tfppy) 2 (ttppy) 2 (tntppy) Wavelength (nm) Fig. S4 Emission spectra of Ir(ppy) 2 (Stpip), Ir(tfppy) 2 (Stpip), Ir(ttppy) 2 (Stpip) and Ir(tntppy) 2 (Stpip) in degassed CH 2 Cl 2 solutions (5 1-5 mol L -1 ) at 77 K. Normalized Intensity (a. u.) (ppy) 2 (tfppy) 2 (ttppy) 2 (tntppy) Wavelength (nm) Fig. S5 The PL spectra of Ir(ppy) 2 (Stpip), Ir(tfppy) 2 (Stpip), Ir(ttppy) 2 (Stpip) and Ir(tntppy) 2 (Stpip) dopants with the host.
5 1 (ppy) 2 1 (tfppy) 2 Model ExpDecay1 Equation y = y + A1*exp(-(x-x)/t1) Counts Model ExpDecay1 Equation y = y + A1*exp(-(x-x)/t1) Plot 1-decay y ± x ± -- A ± -- t ± Reduced Chi-Sqr R-Square (COD).9949 Adj. R-Square.9948 Counts Plot 2-decay y ± x ± -- A ± -- t ± Reduced Chi-Sqr R-Square (COD) Adj. R-Square Time ( s) Time ( s) 1 (ttppy) 2 1 (tntpy) 2 Counts Time ( s) Model Equation Plot ExpDecay1 y = y + A1*exp(-(x-x)/t1) 3-decay y ± x ± E8 A ± E8 t ± Reduced Chi-Sqr R-Square (COD) Adj. R-Square Counts Model ExpDecay1 Equation y = y + A1*exp (-(x-x)/t1) Reduced Chi-S qr Adj. R-Square Value Standard Error 4-decay y decay x E8 4-decay A E9 4-decay t Time( s) Fig. S6 The lifetime curves of Ir(ppy) 2 (Stpip) (τ = 2.86 μs), Ir(tfppy) 2 (Stpip) (τ = 3.32 μs), Ir(ttppy) 2 (Stpip) (τ = 4.11 μs) and Ir(tntppy) 2 (Stpip) (τ = 3.18 μs) dopant with the host. 1 Power Efficiency (lm W -1 ) 1 1 (ppy) 2 (tfppy) 2 (ttppy) 2 (tntppy) Luminance (cd m -2 ) Fig. S7 Power efficiency luminance (η p L) curves of D1-D4.
6 Fig. S8 The mass spectrum of Ir(ppy) 2 (Stpip).
7 Fig. S9 The mass spectrum of Ir(tfppy) 2 (Stpip).
8 Fig. S1 The mass spectrum of Ir(ttppy) 2 (Stpip).
9 Fig. S11 The mass spectrum of Ir(tntppy) 2 (Stpip).
10 Fig. S12 The 1 H NMR spectrum of Ir(ppy) 2 (Stpip). Fig. S13 The 1 H NMR spectrum of Ir(tfppy) 2 (Stpip).
11 Fig. S14 The 1 H NMR spectrum of Ir(ttppy) 2 (Stpip). Fig. S15 The 1 H NMR spectrum of Ir(tntppy) 2 (Stpip).
12 Fig. S16 The 13 C NMR spectrum of Ir(ppy) 2 (Stpip). Fig. S17 The 13 C NMR spectrum of Ir(tfppy) 2 (Stpip).
13 Fig. S18 The 13 C NMR spectrum of Ir(ttppy) 2 (Stpip). Fig. S19 The 13 C NMR spectrum of Ir(tntppy) 2 (Stpip).
14 Fig. S2 Single crystal structure of Ir(ppy) 2 (Stpip). Fig. S21 Single crystal structure of Ir(tfppy) 2 (Stpip).
15 Table S1 Crystallographic data of Ir(ppy) 2 (Stpip) and Ir(tfppy) 2 (Stpip). Ir(ppy) 2 (Stpip) Ir(tfppy) 2 (Stpip) Formula C 46 H 36 IrN 3 P 2 S 2 C 48 H 34 F 6 IrN 3 P 2 S 2 FW T (K) Wavelength (Å) Crystal system Monoclinic Monoclinic Space group P 2 (1) /n P 2 (1) /c a (Å) (9) (5) b (Å) (8) (7) c (Å) (1) (1) α (deg) 9. 9 β (deg) (1) (1) γ (deg) 9. 9 V (Å 3 ) (4) (3) Z 4 4 ρ calcd (Mg/m 3 ) μ (Mo Kα) (mm -1 ) F () Reflns collected Unique Data/restraints/params 8811 / / /18/559 GOF on F R 1a, wr b 2 [I > 2σ(I)].33, ,.86 R 1a, wr b 2 (all data).494, ,.94 CCDC NO R a 1 = F o F c / F o. wr b 2 = [ w(f 2 o F c2 ) 2 / w(f o2 )] 1/2
16 Table S2 Selected bond lengths and angels of Ir(ppy) 2 (Stpip) and Ir(tfppy) 2 (Stpip). Ir(ppy) 2 (Stpip) Ir(tfppy) 2 (Stpip) Selected bonds Bond lengths (Å) Selected bonds Bond lengths (Å) Ir1 C46 2.1(4) Ir1 C7 2.16(5) Ir1 C (4) Ir1 C3 2.28(5) Ir1 N3 2.54(3) Ir1 N3 2.56(4) Ir1 N2 2.63(3) Ir1 N5 2.6(4) Ir1 S (9) Ir1 S (12) Ir1 S (1) Ir1 S (13) Selected angels ( o ) Selected angels ( o ) C46 Ir1 C (14) C7 Ir1 C (19) C46 Ir1 N3 8.61(14) C7 Ir1 N (18) C45 Ir1 N (14) C3 Ir1 N3 8.31(18) C46 Ir1 N (14) C7 Ir1 N5 8.26(18) C45 Ir1 N2 8.25(14) C3 Ir1 N5 93.4(18) N3 Ir1 N2 17.5(12) N3 Ir1 N (17) C46 Ir1 S (11) C7 Ir1 S (14) C45 Ir1 S1 87.5(1) C3 Ir1 S (14) N3 Ir1 S (9) N3 Ir1 S (11) N2 Ir1 S1 92.2(9) N5 Ir1 S (11) C46 Ir1 S (1) C7 Ir1 S (15) C45 Ir1 S (1) C3 Ir1 S (14) N3 Ir1 S (9) N3 Ir1 S1 91.7(12) N2 Ir1 S (9) N5 Ir1 S1 94.8(12) S1 Ir1 S2 1.37(3) S4 Ir1 S (4)
17 Table S3 Data of theoretical calculation of orbital energy level and electron cloud distribution Composition (%) Complex Orbital Energy/e V E gap /ev Ir Main ligands Ancillary ligands Ir(ppy) 2 (Stpip) HOMO LUMO Ir(tfppy) 2 (Stpip) HOMO LUMO Ir(ttppy) 2 (Stpip) HOMO LUMO Ir(tntppy) 2 (Stpip) HOMO LUMO
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